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Squires Partners

Information Technology Manager - work in the Cayman Islands!

Windsor, ON, Canada

Full-time

Within 25 km of Windsor · About 2.4 km from the city centre

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Job details

Job type: Full-time
Apply by: Nov 22, 2026
Posted: Oct 23, 2026

Original job description

Information Technology Manager – Cayman Islands

Relocate to live and work in beautiful Grand Cayman! Grand Cayman is home to a large international community, including many expatriates from Canada and around the world.

Competitive TAX-FREE Salary | Relocation Assistance | Caribbean Lifestyle

An established Cayman Islands organization is seeking an experienced, hands-on IT Manager to oversee the technology environment supporting its primary retail operation and related businesses.

Key Qualifications

The employer is particularly interested in candidates holding current industry certifications, including:

VMware: VCP-DCV (or equivalent VMware certification)
Microsoft: Windows Server administration (AZ-800/AZ-801 or equivalent)
Microsoft 365: Relevant administration certification
Microsoft Exchange: Additional certification or specialized training would be an asset

The ideal candidate is expected to have at least 10 years of hands-on systems administration and IT infrastructure experience, including strong practical experience with VMware, Windows Server, Microsoft 365 and Exchange.

The Role

Reporting to the CFO, this is a hands-on technical position focused on managing and supporting the organization's IT environment rather than managing a team.

The technology environment includes Windows Server, Active Directory, Microsoft 365, hybrid Exchange, VMware ESXi/vSphere, Veeam backup and disaster recovery, Ubiquiti UniFi and Cisco networking, Synology NAS, and various retail and business systems across several sites.

Responsibilities include day-to-day systems administration, troubleshooting, infrastructure upgrades, IT projects, security, backups, disaster recovery and coordination with external service providers. Some after-hours and on-call availability will be required.

Relocating to the Cayman Islands

This is a permanent, full-time position based on-site in George Town, Grand Cayman. Applicants should be genuinely interested in a move and in a position to relocate to the Cayman Islands with relative ease.

Our client offers a competitive TAX-FREE salary, health insurance, pension and other benefits, ongoing training and certification support, relocation assistance and an employer-arranged work permit.

Interested in learning more?

Please apply or contact Jason Squires for further details or a confidential discussion.

Apply About employer

More about this job

Responsibilities

Manage and support the organization's IT environment across its retail operation and related businesses, including systems administration, troubleshooting, infrastructure upgrades, and IT projects. Oversee security, backups, disaster recovery, and coordination with external service providers, with some after-hours and on-call availability.

Requirements

Candidates should have at least 10 years of hands-on systems administration and IT infrastructure experience, with strong practical experience in VMware, Windows Server, Microsoft 365, and Exchange. Current industry certifications are particularly sought, including VMware VCP-DCV or equivalent and relevant Microsoft administration certifications; Exchange certification or specialized training is an asset.

Skills

Systems Administration
IT Infrastructure Management
VMware
Windows Server Administration
Microsoft 365 Administration
Microsoft Exchange
Active Directory
Network Administration
Backup and Disaster Recovery
IT Security
Troubleshooting
Infrastructure Upgrades
IT Project Coordination
Vendor Coordination

Benefits

Health Insurance
Pension
Relocation Assistance
Ongoing Training
Certification Support
Employer-Arranged Work Permit

Visa sponsorship

Detected

Hiring contact

Jason Squires

Keywords

VMware
VCP-DCV
Windows Server
AZ-800
AZ-801
Microsoft 365
Microsoft Exchange
Active Directory
Hybrid Exchange
VMware ESXi
VMware vSphere
Veeam
Backup and Disaster Recovery
Ubiquiti UniFi
Cisco Networking
Synology NAS
Systems Administration
IT Infrastructure
Retail Systems
IT Security
Infrastructure Upgrades
IT Projects
External Service Providers
On-Call Support
Work Permit

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